


5 Sexy Outfits Annie Wore (and One Jeff Helped Her Out Of)

by rufeepeach



Category: Community
Genre: F/M
Language: English
Status: Completed
Published: 2012-06-04
Updated: 2012-06-04
Packaged: 2017-11-06 20:03:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,070
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/422679
Author URL: https://archiveofourown.org/users/rufeepeach/pseuds/rufeepeach
Summary: <blockquote class="userstuff">
              <p>Annie likes to look the part, and Jeff is inclined to agree.</p>
            </blockquote>





	5 Sexy Outfits Annie Wore (and One Jeff Helped Her Out Of)

One - Professor  
  
“Okay, class, as Professor Williams is absent today, I’m taking his place!” Annie strode confidently into the classroom, broad grin on her face, trying not to burst with excitement.  
  
Jeff, lounging in the back row, found that he was actually surprised. Of course, he didn’t let it show. Just like he didn’t show how Teacher Annie had suddenly shot up onto his Top Ten Fantasies.  
  
He decided not to think too hard about how she had come to _own_ that list.  
  
She walked between the tables and handed out the test papers, and he caught her eye. She obviously hadn’t noticed him, because her eyes suddenly widened and she threw his test down and walked away very quickly. She was probably afraid that their friendship would affect her integrity or something like that, knowing her.  
  
She settled herself primly behind the desk and folded her arms, “You have one hour, exam conditions,” Jeff could see her excitement at playing teacher threatening to spill over, and tried not to find it adorable, “You may begin.”  
  
He looked down at his paper, saw it was multiple choice, and got to work.   
  
Then he glanced up, the same time she did, and their eyes met.  
  
‘Jeff!’ She mouthed, and looked pointedly down at her own work, ‘Work!’  
  
Since when could they communicate perfectly without sound?  
  
He smirked, and admired the way her cheeks flushed just a little. He looked back down and got on with the test, victorious.  
  
Somehow, even from the back of the room, he could hear her legs cross and recross under the desk. He looked up again and saw her leaned over her work, enough so that her low-cut top posed a major distraction.  
  
 _Eyes down, Winger!_  
  
He handed her his test on his way out, and they were alone in the classroom. “Nice outfit.”  
  
 She looked down at her business-y black skirt and blouse, and patted her up-do. “Thanks! Not to travel agent?”  
  
“No it’s… perfect.” He could feel his Annie-smile coming on, the disgustingly schmoopy, warm look he couldn’t control sometimes.  
  
“Well… thank you.” She was suddenly very, very close, and he could feel the warmth of her body.  
  
“Right… bye!” Self control almost in tatters, Jeff fled.  
  
\---  
  
Two - Nurse  
  
Jeff coughed pathetically, convinced he was dying.  
  
“Okay, open wide.” Annie held a spoonful of mushed-up vegetable soup near his mouth, and he shot her a glare. She just giggled, “Come on, here comes the airplane!”  
  
“I can feed myself.” His voice came out bunged and hoarse, as he snatched both spoon and bowl away from her, expecting her to leave. She stayed, sat on the side of his bed, watching him.  
  
“What?”  
  
“Nothing.”  
  
“I don’t need a babysitter.”  
  
“Then stop acting like a baby.”  
  
“I’m _dying_.”  
  
“No, you’re not.” Annie, always practical, smoothed her crisp white apron and gave him a stern look, “Now eat your soup and get some sleep.”  
  
She got up and drew the curtains. She stood on her tip-toes to grab another blanket from on top of the wardrobe, and even in his feverish state, Jeff was able to admire the view of her legs extending long and pale and perfect under her skirt.  
  
“Why?”   
  
“Hmm?” She turned, brandishing a stack of blankets, “You need to break your fever.” She walked back to the bed and did a fine job of tucking him in.  
  
“No, why the outfit?” He gestured to her blue skirt and matching top, and white apron and headband. With the cool flannel she was placing on his forehead, she looked like the sexiest Florence Nightingale he’d ever seen.  
  
“Outfit?” She frowned, “Oh, the apron! When you said ‘aaagh, I’m dying and I’m taking you all with me!’ I didn’t know how messy it would be, and I like this skirt.”  
  
He nodded, and even his neck hurt. She leaned down, and kissed the flannel on his forehead, seemingly without thinking about it, “Night.”  
  
“Night.”  
  
She was just a slim silhouette in the doorway when he said, half asleep, “Annie?”  
  
“Yeah?”  
  
“Stay?”  
  
“I’m already set up on the couch.” He could hear the smile in her voice as he drifted off to sleep.

  
\---

  
Three - Waitress  
  
Jeff hurried inside the bar, out of the rain, and took seat at the bar, “Scotch, neat.” He addressed the back of the waitress’s head, and nearly jumped out of his skin when he she turned and he recognised her.  
  
“Hey, Annie-”  
  
“Jeff!” She squeaked, and pressed a finger to her lips, silencing him, “I’m not Annie here.” She whispered, “I’m Caroline Decker!”   
  
“Oh!” Jeff nodded, understanding, “You can get away with that?”  
  
“Well…” Annie looked uneasy, “I can work late nights, and weekends, and people like to be served with a smile, and I work for reduced pay.”  
  
“Ahh.”  
  
“So, scotch, was it?” Annie fetched a bottle of JDs and filled a glass.  
  
“Um, yeah. An-…” At her stare he broke off “I mean, Caroline, isn’t this a school night? Shouldn’t you be safely away in your room, studying like there’s no tomorrow?”  
  
“Well, I need the money. When rent requires bar work or Dildopolis, you realize where your priorities lie.”  
  
His eyes widened again, the image of Annie + Adult Toys suddenly flooding his brain.  
  
“Dildopolis…” He drawled, eyebrow raised.  
  
“Yeah, my apartment is kinda right above it. I told you my neighborhood sucked.”  
  
“You weren’t kidding.”  On a Tuesday night, the bar was empty but for the two of them, and a couple of stoners in a back corner. “Join me?”  
  
Annie shrugged, “Why not?” She bustled around, made herself a Long Island ice-tea, flourishing it with a long straw,  “So what’re you doing here on a school night? Date cancelled?”  
  
“No, I was just driving around, bored, whatever.”  
  
“How come?”  
  
“What’s with the curiosity?”  
  
“What’s with the evasiveness?”  
  
“Maybe I don’t want to explain my personal life to an underage waitress.”  
  
“What’s to explain?” Annie took a long suck of her drink, and Jeff was momentarily distracted by her full, red lips wrapped around the straw. Either the whiskey-goggles setting in super early, or she was looking even better than usual tonight.   
  
“I’m supposed to be a high-powered lawyer in an international firm. I’m supposed to defeat the DA and bring in more money than I know what to do with, and score on a regular basis. Greendale has taken all my old powers, it’s like Kryptonite!”  
  
Annie’s face was a little flushed - she couldn’t really hold her liquor, he remembered - but redder still from anger. “Well, boo-hoo Jeff Winger!”  
  
“I’m sorry?”  
  
“I know you had this great, dishonest, silver-tongued lifestyle going on back there, but you got busted, mister, and that’s the end of it. Life’s been this way for near-on two years now, and if you can’t deal with that, then I’m sorry but that’s just too damn bad!”  
  
“Annie-”  
  
“And another thing!” She was obviously on a roll now, “I’m sorry, but I can’t see how you not getting laid every other night by one random floozy after another is a bad thing!”  
  
He stifled a chuckle, “Did you seriously just say ‘floozy’?”  
  
“Yeah, I did, how else do you describe Quendra-with-a-Q-U or Gwynnifer? Jeff, if you’re not careful you’ll grow into Pierce, and no-one wants that. Did you ever thing Greendale might have done you a favour?”  
  
“Sorry, Annie.” He expected to feel irritated or even angry at her ranting, but he just found it _adorable_. Maybe because he’d accepted most of this stuff over a year ago, and he just enjoyed moaning every once in a while. Especially when Annie - who’s dark apron was almost as sexy as her white nurse’s one - was there to yell at him for it.

\---

Four - Cop  
  
April Fool’s Day was here again, and despite the Dean’s hopes to the contrary, pranks ran rife through the campus. He was forced to hire extra security again, and Annie was happy to sign up for a second year.  
  
“Come on, Jeff, it’s fun!” She was using her Disney eyes to full advantage.  
  
“Last year, you smacked my head against a desk!” he protested, trying to walk away from her. She did that little dodge and dive maneuver she was so good at and popped up back in front of him again.   
  
“I won’t be able to do that if you’re my partner!” She chirruped, “Please, Jeff? I really need help here and Britta doesn’t believe in authority and Troy and Abed have something planned and Shirley didn’t want a repeat of last year and Pierce is… Pierce. So that leaves you. Please?” She brushed her chest against his arm, completely on purpose, “The Dean’ll let you out of classes all day. You’ll miss the Theoretical Phys. Ed test.”  
  
He sighed, and she obviously knew she’d won. “Fine. I’ll stand and watch you do all the work and pretend to help. Deal?”  
  
“Deal!” She squealed, excitedly, and hugged him on impulse. Then she cleared her throat, a little awkwardly, and hurried away.  
  
It was a mistake, Jeff realised later, to ever give in to those eyes. Because when Annie showed up the next day in her cop outfit, so much less conservative than last year, he could think of about ten things that were probably illegal in most states and certainly not allowed on campus, all relating to Annie and the removal of that outfit.  
  
Except the handcuffs. They could stay in 9/10 of his ideas.  
  
“Uh… we were supposed to dress up?” He had worn slightly darker clothes than normal, and refused the Greendale cap on the grounds of how badly it would screw with his hair, but Annie’d gone all out. Her skirt was shorter - to allow for ease of movement, he guessed -, her dark blouse was tight and fitted, and he was sure she had bought the hat and cuffs from the shop under her apartment. With the black boots she had to have borrowed from Britta, it all made a rather wonderful and entirely inappropriate image.  
  
“Well, I did. Wanna look the part, you know?”  
  
“Uh, sure.” Polysyllabic words were an issue, so he decided to just follow his - entirely oblivious - partner out to patrol the campus  
  
They caught every male criminal they found that day, mainly because when Annie ran in those heels, and that shirt, they were so busy staring at her to bother to run away themselves.

\---  


Five - Cheerleader  
  
There was no warning, no bulletin, no news item on the radio that morning to prepare Jeff for what met him when he finally arrived at college that morning.  
  
The cheerleaders were holding their try-outs, after Tiffany Hale broke her leg the week before. That was a sight treasured by all Greendale males: the hottest girls on campus bouncing about in tiny uniforms.  
  
Jeff moved to the front of the assembled crowd, finding himself next to Duncan. “Ahh, I love America.”  
  
“For once, Duncan, I think we agree.” Jeff eyed the new recruits appreciatively, eyes resting on a buxom brunette on the front row.  
  
“Now, you have good taste.” Duncan commented, as the girl they were both staring at turned around, “That is one hot mama right there.”  
  
Annie’s eyes met his, and she waved a little with her pom-pom, grinning happily. Jeff glanced around, irrationally panicked, and saw every guy in sight’s eyes rested on her, jumping and shaking in her teeny-tiny cheerleader outfit.  
  
The routine finished, and the squad broke apart. Without really thinking about it, Jeff moved over to Annie and pulled off his coat, wrapping it around her and hurrying her inside, into a deserted corridor.  
  
Somehow, her running around weeks before as the sexiest campus patrol officer ever hadn’t worried him. Probably because then, at least, she didn’t seem to be intentionally flaunting herself in front of everyone. Now, however, it was obvious she didn’t have a problem with guys like Chang, Duncan and Starburns staring at her like that, and some deep, dark, repressed caveman urge made Jeff anything but okay with that.  
  
“Ah- hey, Jeff. What’s up?”  
  
“What’s up?” He mimicked, “That outfit has to be at least two sizes too small.”  
  
“No, it’s a 6, I wear a 6.” She shrugged off his coat, and he replaced it just as quickly, “Jeff!” She scolded, “What is wrong with you today?!”  
  
“What’s wrong with _me_? Annie, you may not know this, but every man here is staring and not at your face.”  
  
“God! How can you be so patronizing? I’m not a little kid, Jeff, I don’t need you to protect me!”  
  
“Um, yeah, you do, because I promise, at least half the guys here are not thinking with their heads right now.”  
  
“Oh, yeah, only half? What about you, Jeff, what are you thinking with right now?” She got up in his face, threw off the coat, and put her hands on her hips, “If guys want to look at me, if they think I look good, then that’s flattering, and my business. Not yours.”  
  
“Oh, it’s my business.”  
  
“How? How is this anything to do with you? Just because you look at me like a four year old doesn’t mean everyone else has to!”  
  
“Because-”  
  
“Because what?!” They were right up in each other’s faces now, breathing hard, and then Jeff’s mouth was crushing hers and it was all lips and teeth and tongue and Annie was melting into him for just a second.  
  
Then he came to his senses, pushed her away, and with a last, stunned look, he marched away down the corridor.

\---

  
Six - Princess  
  
It was the most conservative Cinderella costume he’d ever seen, and all he could think was how fast he could rip it off her.  
  
She’d been dancing with Troy and Abed all night, laughing and twirling and generally enjoying her friends. She’d even danced with Britta, in her Xena costume, although the concentrated attention of Leonard, Pierce and Starburns soon cut that short.  
  
Jeff didn’t dance. He just stood in a corner, pretended to text, and watched a girl half his age, dressed as a fairytale princess, taunt and tease him without even making eye contact.  
  
Because she knew what she was doing. Whenever she thought he wasn’t looking, she would sneak a glance to make sure he hadn’t left yet, and she’d declined every offer of a ride home.   
  
Finally, purposefully, she looked up over Troy’s shoulder and caught Jeff’s eye. And held it.   
  
Then she licked her lips.  
  
It was the straw that broke the back of Jeff’s self-control. He marched across the dance floor, pushed Troy out of the way, and grabbed Annie’s wrist.  
  
He swept her into his arms, bridal style, as soon as they were out of the doors. Her feet didn’t touch ground until they were in his car, kissing like the world was ending, a tangle of legs and arms.  
  
He finally pushed her away, eliciting a little mew of disappointment, “What’s up?”  
  
“We need to get back to my place. Our first time will not be in the back of my car.”  
  
“Oh.” She smiled.  
  
He drove quickly, and they were back faster than he could have imagined.   
  
Up in his apartment, they didn’t break contact the whole way to the bedroom, her hands pulling at his hair as they kissed slowly and thoroughly.  
  
He finally broke their kiss and stood her still in the darkness of the bedroom. He moved around behind her and moved her hair over one shoulder, kissing her neck as he undid the catches on the back of her dress, kissing a line down her spine with every new inch of skin revealed. Finally, he paused, and pulled her dress down so that it fell in a sky-blue silky puddle at her feet.  
  
He could hear her breathing, shallow and fast, in the darkness. He stepped back to admire his handiwork, and thought that of all the outfits he’d seen her wear, white lacy underwear and the orange glow of the street outside was the best by far.  
  
He’d stripped his own costume - something like a cross between a pirate and Zorro - off within moments, and then he was pressing her into the mattress, pinning her arms above her head as he ravished her neck, her collar bone, the taught red peaks of her breasts, her bra and panties having flown off her somewhere between him getting naked and getting on top of her..  
  
“I guess you liked the costume then?” She giggled, breathlessly, as he slipped one finger deep inside her, feeling how wet she was already for him, seeing the deep blush staining her cheeks as he found the evidence of his effect on her.  
  
“I’d say it was mutual.” He noted, as he moved up over her and slid up inside her.  
  
“Ahh!” She half screamed, half panted, as he moved all the way inside her, and held himself there, encased in hot, wet, velvet tightness, letting her get used to his considerable length before pulling out and ramming home again, setting up a punishing rhythm that soon had her crying out into the night, him groaning into the warm skin of her neck.  
  
“Jeff!” she cried out, and he felt himself grow even harder at the sound of his name, moaned from her lips. “Ah, ah, yes, there, please, right there!”  
  
“Annie!” She ran her hands down his back, scoring her nails into the flesh there, and the stinging pain felt better than he ever thought it could.  
  
“So close, oh God, so close, please!”  
  
“Please what?” Some urge, born of Satan, Jeff was sure, came over him. He had to hear her say it, “What do you want, Annie?” He slowed down, pulling out further and further and then pushing right back home again, harder than before.  
  
“Oh God!” She panted, head thrashing. Her eyes opened a little, looked up unto his smirking face, “Please!”  
  
“Please what?” He prompted again.  
  
“Let me come. Oh God! Please let me come!”  
  
“As you wish.” He increased is pace until all she could do was moan and make incoherent noises, coming apart in his arms as her orgasm crashed through her, her nails digging even deeper into his shoulders.  
  
He followed soon after, pumping a few more times into her limp, post-coital body, until he came hard with a deep grunt and collapsed next to her, slinging one arm over her and smiling sleepily.


End file.
